549-91-7

Basic information

• Product Name: (2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde
• Synonyms: (2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde;Protoemetine
• CAS NO: 549-91-7
• Molecular Formula: C₁₉H₂₇NO₃
• Molecular Weight: 317.42258
• Mol File: 549-91-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde(549-91-7)
• EPA Substance Registry System: (2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde(549-91-7)

Safety Data

• Hazardous Substances Data: 549-91-7(Hazardous Substances Data)

Usage

Description

An oily base obtained from the bark of Cephaelis Ipecacuanha (Brot) A. Rich, the alkaloid is characterized as the perchlorate which forms crystals of the monohydrate from aqueous EtOH, m.p. 140-2°C or 193-5°C (dry). This salt has [α]D - 10.9° (c 3.13, EtOH) and gives an ultraviolet spectrum in ethanol with two absorption maxima at 232 and 283 mJ1. The base contains a formylmethyl group and yields a crystalline semicarbazone, m.p. 168-9°C. The optically inactive base has been synthesized and is also a colourless oil, giving a semicarbazone, m.p. 185-6°C.

References

Battersby, Davidson, Harper.,J. Chem. Soc., 1744 (1959) Battersby, Harper., ibid, 1748 (1959) Synthesis: Santay, Toke, Kolonits., J. Org. Chem., 31, 1447 (1966)

Upstream product

• 7344-78-7 (-)-protoemetinol 
• 122937-65-9 (-)-(2R,3R,11bS)-2-(2-Benzyloxyethyl)-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxy-11bH-benzoquinolizidine 
• 1325690-27-4 C₁₅H₁₈O₅ 
• 1325690-29-6 C₁₉H₂₆O₆ 
• 123001-21-8 (+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone 
• 1361016-14-9 C₁₉H₂₅NO₃ 
• 1361016-21-8 C₁₉H₂₇NO₄ 
• 1357385-46-6 methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate 
• 1357385-48-8 {(2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl}methanol 
• 1357385-49-9 (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-3-vinyl-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 

Downstream Products

• 522-99-6 isoemetine 
• 483-18-1 emetine 

Relevant articles and documents

A Chiral Pentenolide-Based Unified Strategy toward Dihydrocorynantheal, Dihydrocorynantheol, Protoemetine, Protoemetinol, and Yohimbane

An organocatalytic cross-aldol reaction of formaldehyde (formalin) with alkyl aldehydes, followed by the Z-selective Horner-Wadsworth-Emmons (HWE) reaction and immediate lactonization, afforded γ-alkylated pentenolides in good overall yields and excellent

A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: Efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related

Here we present a general and common catalytic asymmetric strategy for the total and formal synthesis of a broad number of optically active natural products from the corynantheine and ipecac alkaloid families, for example, indolo[2,3-a]- and benzo[a]quino

Asymmetric Total Synthesis of (-)-Protoemetinol, (-)-Protoemetine, (-)-Emetine, and (-)-Tubulosine by Highly Stereocontrolled Radical Cyclisations

Both enantiomers of the menthyl half-esters (10) and (23) of ethylmalonic acid were converted into (+)-(4S,5R)-4-(2-benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone (18).A mixture of the trans-(18) and cis-lactones (19) in a ratio of ca. 4:1 was prepared by way of radical cyclisation of the (E)-α,β-unsaturated esters (16), while the former (18) was synthesised with high stereoselection by the cyclisation of the (Z)-esters (26).The lactone (18) was enantioselectively transformed into (-)-protoemetinol (5) and (-)-protoemetine (4), correlated to (-)-emetine (1) and (-)-tubulosine (3).